HCID 23567019, compound → HCID 10221997, compound

HRID 1797214Notes

Reaction equation

HRID 1797214 reaction equation
[F:1][C:2]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]([OH:27])=O)=[C:20]([N+:28]([O-])=O)[CH:19]=2)=[CH:14][CH:13]=1)([CH3:11])[CH2:3][NH:4][S:5]([CH:8]([CH3:10])[CH3:9])(=[O:7])=[O:6]>C(O)C.OS(O)(=O)=O.[Zn]>[F:1][C:2]([C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:19]=[C:20]3[C:21]([CH2:24][C:25](=[O:27])[NH:28]3)=[CH:22][CH:23]=2)=[CH:16][CH:17]=1)([CH3:11])[CH2:3][NH:4][S:5]([CH:8]([CH3:9])[CH3:10])(=[O:6])=[O:7]

Participants

5

Reactant 1

HCID 23567019HCID 23567019, compound

Product 1

HCID 10221997HCID 10221997, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 702EthanolSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of {4′-[1-fluoro-1-methyl-2-(propane-2-sulfonylamino)ethyl]-3-nitro-biphenyl-4-yl}-acetic acid (0.311 g, 0.71 mmol, prepared in example 48) dissolved in Ethanol (4.0 mL)/50% H2SO4 (3.0 mL) at ambient temperature then heated to 90° C. is added Zn (0.186 g, 2.84 mmol) in divided portions over 30 minutes. Heating and stirring is continued for 2 h after addition of the Zn. The mixture is allowed to cool to ambient temperature. It is then extracted (EtOAc) and the EtOAc is extracted with 5% NaHCO3, washed with brine, dried (MgSO4), filtered and the filtrate concentrated in vacuo. Chromatography of the residue (silica gel, EtOAc/hexane) provides the title compound.

Workup

  1. temperatureHeating
  2. temperatureto cool to ambient temperature
  3. extractionIt is then extracted (EtOAc)
  4. extractionthe EtOAc is extracted with 5% NaHCO3
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-b8dce4ae714a44eeb24bf5b9aade6527
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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